Pittsfield · Berkshire County, MA
Date night in Pittsfield
Scout analyzed 49 Pittsfield places and surfaced the ones that actually fit date night.
Places analyzed
49
Matches
24
Typical spend
—
Typical visit
1.3 hr
Scout-verified spots
Food & Drink
RARE 297 Steakhouse
Food & Drink
Proprietor's Lodge
Food & Drink
Chocolate Springs Cafe
Food & Drink
Otto's Kitchen & Comfort
Hearty American breakfast, lunch & dinner served in a relaxed dining room with big front windows.
Lenox
Haven
Upscale American breakfast & lunch cafe with an in-house bakery & patio seating.
Food & Drink
No. Six Depot Roastery & Cafe
House-roasted coffee & simple fare served in a rustic-chic cafe with a gallery of local art.
Food & Drink
District Kitchen & Bar
Intimate tavern featuring seasonal American fare in a modern setting, plus craft brews & cocktails.
Food & Drink
La Fogata | Colombian • Latin
Informal eatery offering traditional Colombian & Latin American platters & a global beer list.
Food & Drink
RJ'S RESTAURANT SEAFOOD/CHOPS/PASTA
Food & Drink
Sibaritas Restaurant Inc
Outdoors
Mount Greylock State Reservation
With hiking & a summit road in season, the highest point in the state offers 60- to 90-mile views.
Food & Drink
Patrick's Pub
Irish-style bar offering hearty American pub eats & brews on tap in a cozy, wood-&-brick setting.
Food & Drink
Roasted Garlic
Quaint family-owned eatery dishing up wood-fired pizzas, burgers, pastas & sandwiches.
Food & Drink
99 Restaurants
Kid-friendly pub chain offering classic fare like burgers, wings & salads in informal surrounds.
Food & Drink
Zucchini's | Italian
Comfy restaurant offering American & Italian bites such wood-fired pizza, veal marsala & hamburgers.
Outdoors
October Mountain State Forest
Home to the famed Appalachian Trail, this expansive forest offers camping, hiking & a fishing lake.
Food & Drink
Dottie's Coffee Lounge
Upbeat coffee shop offering espresso drinks, light breakfast/lunch fare & jazz brunch on Sundays.
Food & Drink
Mazzeo's Ristorante
Buzzy, family-owned Italian mainstay known for its housemade ingredients and extensive wine list.
Nightlife
Methuselah Bar and Lounge
Rustic-chic eatery & lounge serving organic wines & craft beer paired with local New American fare.
Food & Drink
Applebee's Grill + Bar
Full-service chain bar & grill providing hearty American eats in an informal setting.
Sports & Recreation
Wyndhurst Golf & Club
High-end rooms & suites on 380 acres, plus numerous sports facilities & dining options.
Food & Drink
BB's Hot Spot at The Lantern Bar
Nightlife
Antimony Brewing - Craft Brewery & Kitchen
Nightlife
Hangar Pub and Grill of Pittsfield
Outdoors
Patio, trail, or open-air.
No reservation needed
Walk in tonight.
Book ahead
Book tours and tickets in Pittsfield
Lock in the parts of the plan that sell out — tours, tastings and timed-entry tickets across Pittsfield.
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Make it a night out
Staying over in Pittsfield?
Hotels, resorts and vacation rentals across Pittsfield — book the stay and make a full weekend of it.
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